Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Reaction of Oxymercurials. Synthesis of 6,6-Dimethyl-spiro[2,5]octan-4,8-dione
Katsuhiko IchikawaOsamu ItohTakahisa Kawamura
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1968 Volume 41 Issue 5 Pages 1240-1245

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Abstract

The reaction of oxymercurial of ethylene with dimedone in acetic acid containing perchloric acid, followed by treatment with sodium chloride, gave 2-(β-chloromercuriethyl)-5,5-dimethyl-cyclohexan-1,3-dione. Upon treating this mercurial with an equimolar amount of aqueous potassium hydroxide, 6,6-dimethyl-spiro[2,5]octan-4,8-dione was obtained. Oxymercurial of propylene reacted with dimedone to form a mixture of 4-oxo-2,6,6-trimethyl-2,3,4,5,6,7-hexahydrobenzofuran and 4-oxo-3,6,6-trimethyl-2,3,4,5,6,7-hexahydrobenzofuran under simultaneous demercuration; the mercurial corresponding to that in the case of ethylene could not be isolated.

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